Tour the New Castle Loop with guest blogger Janice Murphy-Henderson!

Hidden alcoves and charming bends line the famous route that locals refer to as the six-mile “New Castle Loop” – a favorite early morning running course that also doubles as an all-day adventure filled with natural beauty, wildlife, historic architecture, and picturesque sea views. This route, listed in many travel guides as one of the best coastal drives in America, is celebrated by bikers, walkers, and runners alike; in my opinion it is best explored by foot. Walking allows an up-close glimpse of tiny crushed seashell driveways, lush gardens, and homes brushed up against the water.


Let’s hit the road, shall we?

Where to Park: Secure a spot at Portsmouth’s municipal parking down the hill from the City Hall. If you happen to be there on a Saturday during the summer, feast your senses on the tastes and smells of the Portsmouth Farmer’s Market.

Start your journey at the small Italian market, Napoli, and buy a cold drink to keep cool on your travels. Continue walking along New Castle Avenue, where you will be greeted by the smell of salt air. Sit a spell on the green bench and enjoy watching the many joggers, dog-walkers, and bikers passing by.

Entering New Castle: As you pass over two causeways into New Castle, you’ll enjoy ocean views and watching people fish, paddle and kayak on the back channels and the Piscataqua River. While strolling throughout this island town, peek around its side streets and admire the pastel-painted homes with lush gardens and magazine-worthy landscaping.


Lunch: Why not stop for a bite at Henry’s Market Café? Enjoy the classic cheddar grilled cheese sandwich and cool down with a refreshing beverage (If you happen to be there on a Saturday, you simply must try one of Henry’s famous sticky buns – they’re divine)!

Ocean Views: Be sure to stop at Portsmouth Harbor Lighthouse – New Hampshire’s only mainland lighthouse, located at the U.S. Coast Guard Station. The lighthouse offers tours on select days during summer months – click here for more information!

Continue on past Great Island Commons for a leisurely swing and a walk down the pier. For another detour, meander along Wild Rose Lane for about half a mile and tour Fort Stark and its secluded beach. If you catch it right, sea glass and tiny crabs will abound at low tide.


The High Life: As you continue along “The Loop”, you will be welcomed by the majestic red roof of the historic and luxurious Wentworth by the Sea Hotel. Walk across the way and through vibrant gardens, to the Marina, for a glance at some of the most dreamy, spectacular yachts. Pop by The Green Bean Cafe (at the Marina) and indulge in a strawberry lemonade over ice; it’s the perfect thirst-quencher for a sunny afternoon!

Sweet Treat: After meandering across the drawbridge and strolling past Wentworth By the Sea Country Club and Golf Course, you’ll find the pot of gold at the end of the rainbow – The Ice House! Be prepared for the smells of fried seafood, burgers, and frappes to lure you in for a true taste of summer in New England.


Adventure: Stroll down the short dusty path to Portsmouth Kayak, where paddleboards and kayaks are available for half or full day rentals.

Libations: After a paddle, scoot next door to BG’s Boat House and sit out on the deck; the views of the back channels are spectacular!

Pass over the “Old Singing Bridge” and tour the South Street cemetery. Explore the grounds for four-leaf clovers and visit the tall monument and resting place of Frank Jones, a historic Portsmouth resident who owned one of the largest breweries in the country – Frank Jones Brewing Company on Islington Street.


There’s so much more to see on future trips around the loop….

-Shoot some hoops at Little Harbour or New Castle elementary schools.

-Walk along the Piscataqua River by The Portsmouth Yacht Club.

-Dine by the water at Latitudes or enjoy a leisurely Sunday brunch at SALT.

-Drop a kayak in along any of the public boat launches.

-Visit Little Harbour Chapel and the Wentworth Coolidge Mansion, both a stroll down Little Harbour Road!

Thank you for giving us a fresh tour of “The Loop” Janice!

About the Author: Janice Murphy-Henderson is a freelance writer and Portsmouth dweller, who enjoys sharing stories about the Seacoast community and its local businesses.

View Janice’s writing here and follow her on LinkedIn, and Facebook!